How I Invest with David Weisburd

By David Weisburd

How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Step... more

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The podcast currently has 236 episodes available.

How I Invest with David Weisburd episodes:

October 08, 2025E223: The Art of Capital Allocation at $86 Billion Scale
What are the real playbooks behind managing an $86B alternative asset platform—and where do the next decade’s returns actually come from?
In this episode, I sit down with Payton Brooks, Managing Director on Future Standard’s Primary Investments team, to unpack the operating system behind a multi-strategy LP: how a combined platform serves both institutions and the wealth channel, why mid-market private equity still offers the best shot at alpha, and how evergreen structures can reduce cash drag while preserving optionality. We cover sourcing (spinouts, emerging managers), what great GPs do in downturns, the co-invest / secondaries / credit toolkit, and the partnership behaviors that earn re-ups across multiple fund cycles.
Highlights:
Future Standard under the FS + Portfolio Advisors merger with ~$86B AUM
How wealth clients access institutional alternatives via structured vehicles
Mid-market outperformance vs. large-cap PE
Operating depth and specialization as scale drivers
Evergreen strategies reducing cash drag
Anchor LPs as credibility signals
Partnership transparency as LP/GP discipline
Co-invest, secondaries & credit augmenting optionality
Patience, credibility & compounding relationships
Guest Bio:
Payton Brooks is a Managing Director on Future Standard’s Primary Investments team, focusing on manager selection and portfolio construction across the private-equity landscape. He joined the firm in 2014, and holds a B.A. from Southern Virginia University and an MBA from the Yale School of Management. Future Standard is a global alternatives platform investing across private equity, credit, and real estate, serving both institutional and private-wealth clients; the firm rebranded from FS Investments in July 2025 following its combination with Portfolio Advisors in June 2023.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Payton Brooks: https://www.linkedin.com/in/paytontbrooks/
Links
Future Standards: https://www.futurestandard.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(0:44) Client base and portfolio construction
(1:40) Differences between high net worth individuals and pension funds
(3:02) Access for high net worth investors to asset classes
(4:05) Characteristics of successful private equity funds and large cap buyouts
(9:21) Evaluating middle market managers and building relationships
(16:40) Utilizing secondaries, co-investments, and internal team structure
(19:01) Traits of elite superstar GPs and repeatable value creation
(23:22) Decision-making process and portfolio construction within the buyout fund
(28:39) Pension fund investment in Evergreen Fund mechanics and benefits
(34:14) Evergreen Fund strategy, market impact, and comparison to drawdown funds
(41:32) Challenges and strategies for emerging managers
(44:02) Securing anchor investors and LP decision-making
(47:58) Importance of time optionality in fund investments
(51:08) Balancing early and late fund investments
(53:20) Career reflections and advice to younger self
(55:23) Enhancing investment knowledge and leveraging partners for insights
(57:06) Closing remarks
...more
58min
October 06, 2025E222: Why 90% of Managers Fail Before Fund 3
Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors?
In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out.
Highlights:
Investor ≠ fund manager: portfolio construction, firm-building, and 10–12 year horizons matter as much as deal picking.
Durability over cycles: sometimes the right move is doing zero deals for ~12 months to avoid overpaying.
Power laws require survival: stay in the game long enough to catch the outliers; size and pacing are part of edge.
LPs as partners, not capital: trust, warm introductions (“trust by proxy”), and over-communication—without “crying wolf.”
Team > solo founder myth: first hires and sequencing reveal how companies will actually be built.
Defense tech arc: from taboo to obvious—examples include ICON (3D-printed homes), Saronic, and Manifest (ex-Palantir).
Data-driven firm design: internal platform (“Unity”) reallocates time from low-yield first meetings to high-conviction winning.
Pilot fund outcomes: Ensemble’s Fund I (pilot) marked ~12×; scaling the model required re-architecting org + software.
Guest Bio:
Conrad Shang is Founder & Managing Partner at Ensemble VC. Previously, he led/managed venture investing at UTIMCO and invested at Norwest Venture Partners and Bain Capital Ventures; earlier he was a consultant at Bain & Company. He’s a Kauffman Fellow and has sat on both the GP and LP sides of the table—experience that informs Ensemble’s product- and data-driven approach to firm building.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Conrad Shang: https://www.linkedin.com/in/conradshang/
Links
Ensemble VC: https://www.ensemble.vc/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:25) Fund management skills beyond investing
(2:06) Time horizons in investments vs. fund management
(4:24) Navigating economic cycles and long-term strategy
(7:06) Venture investing and the power law paradox
(8:24) Emerging challenges for new fund managers
(10:48) Investment timing in defense tech and 3D printing
(11:44) Team dynamics and talent as success predictors
(14:57) Trust-building lessons from UTIMCO
(19:04) The critical role of trust in LP-GP dynamics
(21:21) Treating LPs as partners and the educational aspect
(23:50) Mutual benefits of LP-GP collaboration
(29:55) Fostering trusted long-term LP relationships
(33:46) Transparency and communication with LPs
(36:19) Investment theses and relationship importance
(41:58) Insights from LP experience at UTIMCO
(46:41) Practices of successful GPs
(51:58) Relationship alpha and its impact on venture success
(52:32) Ensemble's Fund One and its approach
(54:16) Data and software in Ensemble's investment strategy
(57:06) Data-driven investment case studies
(1:00:37) Ensemble's Unity platform and efficiency tools
(1:03:04) Using data for informed investment decisions
(1:06:06) Team cohesion and its importance
(1:08:14) Closing remarks
...more
1h 9min
October 03, 2025E221: From Citadel to Family Office CIO: Sid Malhotra’s Investment Lessons
What really happens inside the hidden world of family offices—and why do they invest so differently from institutions?
In this episode, I explore that question with Sid Malhotra, Chief Investment Officer at Kactus Capital, a single family office. Sid reveals how family offices align incentives between principals and investment teams, the advantages of having true “skin in the game,” and why their long-term, absolute-return mindset stands apart from pensions, endowments, and foundations. We also discuss the unique strategic role family offices play—from backing zero-to-one opportunities to leveraging deep sector expertise and networks—and how Sid’s career path, from Citadel to Pritzker Group to his current role, shaped his approach to risk, alignment, and building resilient portfolios.
Highlights:
Alignment over agency: how Kactus ties compensation and co-investment directly to long-term portfolio performance.
Single vs. multi-family offices: why governance, focus, and principal control make a difference
Strategic capital: family offices as early backers of crypto, seed managers, and illiquid opportunities institutions avoid
Lessons from six years at the Pritzker Group: how legacy ownership and manufacturing DNA shape an investment lens
Absolute returns and relative returns: why compounding capital while minimizing losses guides Sid’s philosophy
Preparing for corrections: dry powder, T-bills, and opportunistic offense in market sell-offs
Citadel training: lessons on multi-strategy flexibility, thinking across the capital structure, and risk-reward sizing
The total portfolio approach: blending macro-awareness, bottoms-up selection, and thematic top-down views
Career advice from Booth to CIO: why networking early is as critical as working hard
Guest Bio:
Sid Malhotra is the Chief Investment Officer at Kactus Capital Management, a single family office where he leads all investment activity across public and private markets. Before joining Kactus, Sid spent over six years at the Pritzker Group, helping steward the family’s legacy of business ownership and investing across multiple asset classes. Earlier in his career, he worked at Citadel, gaining multi-strategy and capital-structure investing experience. Sid holds an MBA from the University of Chicago Booth School of Business and a B.A. in Economics from the University of Michigan. He has completed the Value Investing Executive Education program at Columbia Business School and is a Chartered Financial Analyst (CFA) Charterholder.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Sid Malhotra: https://www.linkedin.com/in/sidmalhotra/
Links
Kactus Capital Management: https://www.kactuscapital.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(2:09) Alignment of Interests and Trade-offs in Family Offices
(5:24) Strategic Nature of Family Offices and Learnings from Pritzker Group
(9:30) Focus on Absolute Returns and Criteria for Investment in a Manager
(12:26) Investment Style: Jigsaw Puzzle vs. Treasure Hunt
(14:24) Preparing for Market Corrections and Managing Dry Powder
(18:19) Challenges of Cash Reserves and Strategy during Market Sell-Offs
(22:33) Public vs. Illiquid Investments During Crises and Sources of Alpha
(26:30) Lessons from Working at Citadel and Appeal of Multi-Strategy Firms
(33:04) Impact of Tax Considerations on Portfolio Construction
(35:46) Building a Career and Network Post-Business School
(37:25) Closing remarks
...more
39min
October 01, 2025E220: Why Family Offices Quietly 5x’d Their Alt Allocations
Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices?
In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction).
Highlights:
Four kinds of complexity stopping alts adoption: access, legal/regulatory, reporting (K-1s, non-standard NAVs), and liquidity.
Why operational complexity is the #1 reason many RIAs avoid alts (industry surveys ~40–50%).
The public → private shift: volatility aversion + search for alpha and predictability.
Information asymmetry has widened: trillion-dollar GPs vs. individuals and smaller RIAs—why tooling must level the field.
AI’s role: extract, integrate, and chat with unstructured docs; unified LP workflow from access → diligence → reporting → exit.
RIA reality: clients already bring outside deals/K-1s—consolidated balance-sheet reporting is now table stakes.
Why due-diligence management is the sleeper pain point—and how comparative analytics change decisions
Context for performance: the conversation references Kaplan–Schoar/PME research on PE vs. public markets (as discussed in-episode)
Guest Bio:
David Sawyer is CEO & Co-Founder of Unlimited.ai, an AI-native platform built to orchestrate LP workflows in private markets. Previously, he served as Managing Partner & COO at Legacy Knight, a multi-family office and alternatives platform, and as Managing Director at CAZ Investments. He holds a J.D. from the University of Houston Law Center, studied at the University of Texas at Austin, and is a CAIA charter holder.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
David Sawyer: https://www.linkedin.com/in/david-sawyer-a70ab912/
Links
Unlimited.ai: https://www.unlimited.ai/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(2:54) The role of technology in alternative investment management
(7:31) Strategies for overcoming operational complexity in private markets
(10:21) AI's impact on investor access and information symmetry
(22:07) Standardization and transparency in private market investments
(23:06) Empowering investors with technology and community initiatives
(23:56) Closing remarks
...more
26min
September 29, 2025E219: How Emerging Managers Can Beat Multi-Stage Firms
How do you underwrite pre-seed founders when the only durable asset is the human—before there’s product-market fit?
In this episode, I go deep with Mike Ma, Managing Partner at Sidecut Ventures, on his 30-day “work-alongside” diligence, why he optimizes for action-oriented self-awareness, and how to calibrate coachability—especially in go-to-market—without overfitting to investor bias. We unpack earned secrets, impact theses in education, climate, healthcare, and economic mobility, solo-GP advantages, alignment pitfalls from 2021-era rounds, and the mindset habits he wishes he’d had earlier: “write at a fourth-grade level” and “document your screw-ups.”
Highlights:
The 30-day “grind with them” model: watching founders operate to reduce storytelling bias.
What predicts pre-seed survival: action-oriented self-awareness (execute fast and integrate feedback fast).
Coachability, defined: focus on go-to-market (not deep tech) and respond to market-generated feedback.
Earned secrets: the unfair advantage born at the intersection of novel markets + lived expertise.
Why solo GPs can be more aligned: speed, conviction, and operator empathy at pre-seed.
Valuation ≠ victory: how 2021-style prefs/marks can zero founders despite solid outcomes.
Two habits for builders & investors: write simply and log your mistakes to kill self-deception.
Guest Bio:
Mike Ma is the Managing Partner of Sidecut Ventures, a pre-seed venture firm backing “coachable superheroes” in sectors including economic mobility, digital health, climate, and education. He brings a background as both an investor and operator, with prior roles that span venture capital, operating leadership, and company building. Before founding Sidecut, Mike held leadership positions at firms such as Sway Ventures and Nex Cubed, where he launched fintech initiatives and accelerator programs. He also served as a marketing leader at high-growth startups including Betterment and Own Up, and earlier in his career worked in brand strategy at major financial institutions. A graduate of Harvard University, Mike now applies his experience across investing, operations, and go-to-market strategy to help early-stage founders succeed.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Mike Ma: https://www.linkedin.com/in/michaelwma/
Links
Sidecut Ventures: https://www.sidecut.vc/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(2:30) Assessing and predicting startup success
(7:06) Coachability in startup founders
(13:14) Market size misconceptions and value creation platforms
(22:15) Solo GPs and early-stage startup advantages
(24:14) Innovation and the AI startup landscape
(25:35) Optionality and premium in early-stage funding
(26:48) VC-startup alignment and second-order effects
(29:22) Misalignment in funding and tragic outcomes
(29:50) Thirty-day LLM project insights
(30:41) Asymmetric information and bias in investing
(33:20) Coaching founders and personal advice
(36:57) Closing remarks
...more
38min
September 26, 2025E218: How the Rothschilds, Rockefellers, and Fords Built Enduring Legacies
How can families preserve wealth and well-being across five or more generations?
In this episode, I dive deep into a conversation with James E. “Jay” Hughes, Jr., legendary family wealth advisor and author of five influential books including Family Wealth. Jay shares stories from advising families for over 50 years—why flourishing, not just financial returns, is the real measure of wealth; how families like the Rothschilds and Fords illustrate both triumph and tragedy; and why choosing trustees wisely may be the single most important decision for multi-generational continuity. We explore governance, purpose, philanthropy, Aristotle’s philosophy of flourishing societies, and Jay’s own midlife realization that the true professional question is not “what do you need?” but “how can I help?”
Highlights:
The Rothschild family story: diversification of human, intellectual, and social capital as a foundation for flourishing
Trustee decisions: why one poor choice can unravel a fortune over generations
The Ford family cautionary tale: Henry Ford’s dominance over Edsel, and Henry Ford II’s turnaround
Aristotle’s timeless lesson: no flourishing society without flourishing families
Why purpose and philanthropy grow—not deplete—family wealth
The billionaire pledge: altruism with promise, but outcomes still unproven
Jay’s midlife shift: moving from fulfilling needs to asking, “how can I help?”
His father’s wisdom: knowledge is fungible, courage is invaluable
Guest Bio:
James E. “Jay” Hughes, Jr. is a pioneering family wealth advisor, author, and thought leader who has advised some of the world’s most prominent families for over five decades. A sixth-generation lawyer, Jay began his career in trusts and estates law before dedicating his life to helping families flourish across generations. He is the author of five books, including Family Wealth: Keeping It in the Family, and a frequent speaker on family governance, stewardship, and purpose. Jay has served as a trustee, mentor, and confidant to multi-generational families globally, and is recognized as one of the foundational voices in the modern family office movement.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #assetmanagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Links
About James E. Hughes, Jr.: https://www.jamesehughes.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(1:39) James E. Hughes, Jr.: Background and trust and estate law career
(3:14) Joint decision making challenges in wealthy families
(5:05) Insights on creativity from Zixanth Mahai's book
(9:16) Importance of trustee selection for wealth preservation
(10:48) The Ford family's rise, fall, and legacy transformation
(15:06) Purpose and philanthropy's role in sustaining family wealth
(20:59) Billionaire's giving pledge and its effects on wealth management
(22:32) James E. Hughes, Jr.'s advice for young professionals
(27:07) Closing remarks
...more
28min
September 24, 2025E217: How to Manage $15B: Insights from Sacramento County's Pension Fund
How should a public pension build an active equity and absolute-return program—without diluting alpha or chasing the “hot” manager?
In this episode, I go deep with Brian Miller, Senior Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), on constructing a $6B public-equity book inside a ~$15B plan, sizing managers, and using absolute-return strategies as true diversifiers. Brian reflects on 16 years at Tukman Grossman Capital Management (value, long-term compounding, and staying consistent), the realities of “LP capture” across cycles, and why tracking error isn’t the right risk lens. We unpack manager due diligence (including on-site visits), active vs. passive trade-offs, the global/US mix, and how SCERS uses MSCI Caissa for whole-portfolio visibility.
Highlights:
Lessons from Tukman Grossman Capital Management: consistency, long-term compounding, and fitting the “value/core” role for top LPs.
LP capture in practice: how client flows can force or fund decisions—08/09 liquidity, 2020 upgrades, and who doubles down in drawdowns.
Value vs. growth & small-cap value today: quality dispersion, a smaller small-cap universe, and why “stocks follow earnings” over time.
Portfolio construction at SCERS: shifting to include global vs. pure international; active where it counts with ~half of US equity passive.
Tracking error ≠ risk: focus on downside risk; information-ratio “gotchas” when TE is kept too low.
Absolute Return (7% sleeve): diversifiers (event-driven, macro, market-neutral, derivatives-based arb) that protected in 2022 and target mid-single-digit returns with low vol.
Tooling: how MSCI Caissa gives top-to-holdings look-through across public & private to manage exposures.
Manager selection & diligence: narrow the funnel, visit on-site, prevent false positives, and stay rooted in the original thesis.
Career advice: be a continual learner, build networks early, and develop conviction to hold through criticism.
Guest Bio:
Brian Miller is a Senior (Retirement) Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), where he focuses on Global Public Equity and Absolute Return programs. Before SCERS, he spent 16 years at Tukman Grossman Capital Management in research and portfolio roles. At SCERS he leads manager selection and portfolio construction across public equity and diversifying strategies.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Brian Miller: https://www.linkedin.com/in/brian-miller-205a85/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Introduction
(4:20) Long-term investing and its impact on success
(8:22) Navigating market crises and opportunities
(12:29) Dynamics of small cap value investing
(16:51) Public-private market crossover and manager transitions
(21:10) Manager evaluation and selection insights
(27:46) Investment thesis and building a robust portfolio
(33:44) Diversification and trade-offs in manager selection
(40:50) Role of absolute return strategies
(45:12) Portfolio diversification using MSCI tool
(47:12) Career advice and the importance of networking
(50:31) Investment process and conviction
(50:48) Masterclass on public equity and value investing
(51:01) Closing remarks
...more
52min
September 22, 2025E216: How the $100 Billion Continuation Vehicle Trend Is Changing Private Equity
How can continuation vehicles and independent sponsors unlock structural alpha in private equity when traditional buyouts are struggling with low DPI?
In this episode, I go deep with Paul Cohn, Co-Founder and Managing Partner of Agility Equity Partners, on why continuation vehicles (CVs) and independent sponsor deals are reshaping the buyout landscape. Paul explains how CVs let GPs hold their best companies longer while still providing LP liquidity, why the lower middle market offers outsized return potential, and what makes independent sponsors a fast-growing segment of private equity. We cover alignment dynamics, incentives, real-world deal structures, the findings from the HEC Paris study on CVs, and the lessons Paul has learned over 15+ years investing in this niche.
Highlights:
Continuation vehicle market grew from $7B in 2014 to $70B in 2024, with CVs now making up ~15% of PE exits
Why CVs give GPs a way to hold their best assets longer while still providing LP liquidity
Positive selection vs. adverse selection in CVs — why diligence is key
Example mechanics: GPs rolling carry into CVs and LPs choosing between liquidity or rolling capital
HEC Paris study: single-asset CVs outperformed buyouts on DPI, total value, and dispersion of returns
Why CVs are less risky: tighter dispersion, better alignment, and GPs investing alongside LPs
Growth of independent sponsors: ~1,500 in North America, often more deal volume than traditional funds
Why lower middle market offers more alpha: easier growth, multiple expansion, less competition
Key lessons from Paul’s career: trust your gut on people, make tough changes quickly
Guest Bio:
Paul Cohn is a Partner & Founder of Agility Equity Partners, responsible for sourcing and executing new investments, monitoring portfolio-company performance, and leading intermediary deal sourcing. Before founding Agility, he was Managing Director & member of the Investment Committee at Fort Washington Capital Partners where he led GP-Led Secondaries investments. He also served as a Partner at Mellon Ventures, Mellon Bank’s private equity affiliate (part of its founding team; over $1.3B invested/committed across 100+ companies & 70+ funds). Paul began his career as an investment manager at Westinghouse Credit Corporation, focusing on leveraged buyouts. He holds a B.S. and MBA from the Tepper School of Business, Carnegie Mellon University.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Paul Cohn: https://www.linkedin.com/in/paul-cohn-841914/
Links
Agility Equity Partners: https://www.agilityep.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(1:52) Concerns about dry powder in large buyouts and CV market constraints
(3:03) Explanation and incentives for GPs to use continuation vehicles
(6:04) Diligence, adverse selection, and transitioning to CVs
(10:20) Psychological influences and LP decision-making on CVs
(14:42) Attraction of CVs for LPs and alignment of interests
(16:54) HEC Paris study and private equity returns impact on CV market
(20:55) Evolution of CVs and lower volatility measurement
(23:26) Independent sponsor market growth and transition to raising funds
(27:22) Single asset CV development in the buyout market
(31:11) Allocator concerns and ethics in private equity
(36:29) Conflicts of interest in CVs and advice for young investors
(42:38) Experiences with underperforming team members and learnable lessons in investing
(44:35) Closing remarks
...more
46min
September 19, 2025E215: The Pursuit of Uncorrelated Returns in Venture Capital w/Dan Kimerling
Can venture capital be reinvented to deliver alpha without relying on “heroic assumptions”?
In this episode, I go deep with Daniel Kimerling, Founder and Managing Partner of Deciens Capital, on his mission to build a different kind of venture fund—one focused on highly concentrated, long-duration bets in financial services. Dan explains why Deciens is unapologetically “get rich or die trying,” how his team avoids the venture hamster wheel of markups and momentum rounds, and why he believes the next generation of financial institutions (not just fintech apps) will be the true power-law winners. We cover his philosophy on portfolio construction, long timelines, liquidity vs. exits, and how Deciens publishes its playbooks openly to challenge orthodoxy.
Highlights:
Why Deciens aims to be an uncorrelated alpha stream within venture capital
Radical transparency: aligning with LPs upfront on asymmetric return expectations
Portfolio construction based on computational simulations; choosing concentration over diversification
Targeting 10–15 companies per fund, with a model designed to deliver 5x net returns
The case for financial services as venture’s overlooked mega-sector (20% of global GDP)
Examples from the portfolio: Chipper Cash, Treasury Prime, Tint Insurance, Sidecar, SimplyWise, Generous Energy
The “venture hamster wheel” of markups and why Deciens rejects it
Why liquidity and exits aren’t the same—and why dividends can be just as powerful
14-year fund timelines aligned with LPs like pensions and sovereigns that can go long duration
Deciens as a movement: defying orthodoxy, building with aligned entrepreneurs, and embracing authenticity
Guest Bio:
Daniel Kimerling is the Founder and Managing Partner of Deciens Capital, a first-principles venture firm backed by sovereign wealth funds, endowments, and pensions. Deciens is known for its concentrated focus on financial services—backing both fintechs (like Chipper Cash and Treasury Prime) and next-generation financial institutions (from insurance to asset management). Prior to founding Deciens, Dan co-founded Standard Treasury (acquired by Silicon Valley Bank) and served as GM of API Banking at SVB. A published writer and frequent speaker, he is recognized for challenging conventional VC orthodoxy through essays like Defying Orthodoxy and Betting on Convexity.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #AssetManagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Daniel Kimelring: https://www.linkedin.com/in/dkimerling/
Links:
Deciens Capital: https://deciens.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:52) Deciens's Capital's investment strategy and portfolio examples
(3:00) Deciens's uncorrelated venture strategy and high-risk, high-reward philosophy
(5:24) Managing LP expectations with transparency and communication
(7:00) Nontraditional portfolio construction and computational simulations
(9:45) Process of constructing a portfolio and the conservative approach
(14:13) The potential of financial services companies and ecosystem background
(20:01) Liquidity strategies and exit planning for non-traditional investments
(22:49) Aligning strategy with LPs and venture return competition
(26:28) Small fund size counterarguments and the importance of investment asymmetry
(29:24) Long-duration investment timelines and compound growth
(33:34) Structural alpha advantages and venture fund strategies
(38:23) Learnings from closing Fund three and viewing Deciens as a movement
(42:04) Pitfalls of traditional venture capital models
(46:01) Advice to a younger self on the importance of differentiation
(51:28) Creating durable alpha and structural advantages
(55:11) The impact of the need for validation on investment decisions
(59:21) Aligning firm success with charitable goals and personal motivation
(1:01:22) Closing remarks
...more
1h 2min
September 17, 2025E214: Inside Look into a $14B Multi-Family Office
How can ultra-high-net-worth families invest like endowments—without becoming forced sellers when markets turn?
In this episode, I go deep with Greg Brown, Co-CEO of Caprock, on how a modern multi-family office serves UHNW families. Greg explains why Caprock acts as CFO first and CIO second, forecasting liquidity across complex balance sheets before allocating to private markets. We cover the thresholds for when privates make sense, how to structure portfolios for resilience, the role (and limits) of interval funds, and how Caprock uses pooled scale to negotiate economics and secure access to top deals. We also explore tax-alpha strategies like QSBS, Opportunity Zones, and long/short overlays.
Highlights:
Why Caprock takes a CFO-first, CIO-second approach to wealth management
Liquidity forecasting: mapping every entity, flow, and obligation
Threshold for UHNW privates: around $10M investable assets
How full balance-sheet visibility lets families hold more illiquids
Scale advantages: pooled vehicles with no fees, no carry
Direct access to elite deals: SpaceX, Anduril, Palantir, Addepar, Anthropic, and more
Interval funds: where they fit, where they don’t, for taxable investors
Liquidity buckets: 0–6 months, 6–18 months, and 2+ years
How to avoid becoming a forced seller in downturns
Why Caprock buys secondaries 19 out of 20 times
Tax tools: QSBS, Opportunity Zones, PPLI, 130/30 overlays
Why privates matter: many top companies now stay private longer
Guest Bio:
Gregory Brown is Co-CEO of Caprock, an SEC-registered multi-family office. Previously, he was an active investor and entrepreneur with experience in product & business development strategy, capital formation, and mergers & acquisitions. He holds a B.S. from the University of Idaho and dual MBAs (Columbia Business School and Haas School of Business, UC Berkeley). Greg is based in Seattle. Outside work he enjoys golf, skiing, cooking, and playing drums in a band. He also serves on the board of La Plaza International.
Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at [email protected].
#VentureCapital #VC #Startups #OpenLP #assetmanagement
Stay Connected:
X / Twitter:
David Weisburd: @dweisburd
LinkedIn:
David Weisburd: https://www.linkedin.com/in/dweisburd/
Gregory Brown: https://www.linkedin.com/in/gregorybrown/
Links
Caprock: https://caprock.com/
Questions or topics you want us to discuss on How I Invest? Email us at [email protected].
(0:00) Preview
(0:24) Negotiating better economics through pooled capital
(1:03) Introduction to Greg Brown and Caprock's overview
(2:27) Scale, scope, and roles differentiation at Caprock
(3:46) Client liquidity needs, cash management, and spending
(6:25) Private market investment trends and challenges for high net worth families
(9:53) Managing administrative complexity and client cash flows
(12:13) Caprock's comprehensive service offerings
(13:12) Pooled capital: Advantages, disadvantages, and interval funds
(17:53) Cash flow and liquidity management best practices in family offices
(20:24) Liquidity issues and solutions in private equity markets
(25:33) Secondary market and tax considerations for investors
(28:15) Tax loss harvesting, leveraged equity strategies, and private market investment rationale
(34:35) Diversification and democratization of private markets
(36:45) Opportunities and concerns in private credit and tax planning with PPLI
(40:08) Lessons from founding Caprock and scaling venture co-investments
(45:56) Closing remarks
...more
47min

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